Vacation rentals with a kayak in Connecticut

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Popular amenities for Connecticut kayak rentals

House rentals with a kayak

Top guest favorite
Home in New Milford
4.97 out of 5 average rating, 31 reviews

OWL's PERCH Candlewood Lakefront Rustic Cottage!

JackieRating, 5 stars2 weeks ago
If you're looking for a cute little cottage in the woods near the lake to recharge and relax - this is it! KC provided an extensive list of instructions and to know's, which made check in/check out and all the in-between fool proof. KC was super friendly and responsive as well!
Guest favorite
Home in Woodstock
4.96 out of 5 average rating, 46 reviews

Mid-Century Modern Lakefront Cabin

JacquieRating, 5 stars2 weeks ago
If you’re looking for a serene and restful place to come “home” to after a day out and about…this is the place to stay! The central location allowed us to easily check out Boston, Newport and several Connecticut spots...including a winery & brewery only 10 min away! We also enjoyed down days simply relaxing at Erin’s place….by the fire, lounging by the water or taking a paddle around the lake. And anything you could think of they had…sweatshirts and blankets for outside by the fire, games, fully stocked kitchen for making meals in, steam shower, office space, and more. Our family of four (with adult children) had plenty of space to spread out and have time for ourselves, too. I also really like the mid-century modern decor…very nice touch :) Erin and Jaiden were great hosts. They were very responsive and provided detailed instructions and ongoing communications to ensure our stay was going well. Thanks again!
Guest favorite
Home in Woodstock
4.92 out of 5 average rating, 39 reviews

Country Lake Oasis

AnitaRating, 5 stars4 weeks ago
Memorial Day weekend was cloudy, cool and windy, so my husband, elderly mother and I were especially pleased to have a nicely appointed and welcoming home base for hanging out. From a large screen TV down to the smallest of decorative details, Nicole has thought of everything to make for a relaxing stay. Having rented other places, I particularly appreciated spotless cookware, new bath towels, comfortable beds, and to top it all off an espresso machine! My tea drinking husband kept the electric tea kettle warm all morning. All this and a very nice, peaceful water view with great bird watching. We look forward to returning.
Superhost
Home in East Haven
4.96 out of 5 average rating, 100 reviews

Cozy Beach - Direct Waterfront!

SarahRating, 5 stars6 months ago
This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!
Guest favorite
Home in Old Saybrook
5 out of 5 average rating, 40 reviews

Romantic Couples Retreat with Private Sandy Beach

RajRating, 5 stars3 weeks ago
Fantastic cute spot in Old Saybrook. Key things for future guests to know - there is no A/C in the winter months so the air can get a bit stale / stuffy in the house. Plus there is no washing machine / dryer in the house, so defo bring enough clothes!
Top guest favorite
Home in Brookfield
4.98 out of 5 average rating, 149 reviews

Stay at Old Dorset Farm & create lifelong memories

JessicaRating, 5 stars2 weeks ago
A true gem in Connecticut. The house felt like a family friend was hosting us. It was warm and comfortable, with beautiful attention to details.
Top guest favorite
Home in Milford
5 out of 5 average rating, 104 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

HeidiRating, 5 stars2 weeks ago
We loved Laura and Dana’s Big Easy home by the beach. It was big and comfortable and every detail had been thought about to maximize our enjoyment. Drawers and closets and cabinets were all labeled so we didn’t have to search for anything or guess where anything was. Literally every need had been anticipated! Amazing. The beds and bedding and linens and towels were abundant and soft and comfortable. The kitchen amenities were awesome, from an air fryer, to a full set of bar tools and blender, to great appliances. The decor was happy and cheerful and creative and fun. There were so many places to sit and enjoy, both inside and out. Do not hesitate to choose this wonderful place for a visit of any length. You will love it!
Guest favorite
Home in New Fairfield
4.97 out of 5 average rating, 76 reviews

Hilltop Retreat- Lakefront with Dock

JoeRating, 5 stars3 months ago
Our stay included spending family time in front of the fireplace watching Disney shows and with time spent enjoying meals around the cozy kitchen table. Enjoyed our stay very much and hope to go back one day

Cottage rentals with a kayak

Top guest favorite
Cottage in Groton
4.96 out of 5 average rating, 318 reviews

Charming Historic Schoolhouse on Mystic River

KarenRating, 5 stars1 week ago
We had such a fantastic stay at this special home right on the river in lovely Mystic! It came stocked with everything we needed for a fun couple’s getaway. Gerard was so friendly and accommodating - we felt right at home. Can’t wait to return!
Top guest favorite
Cottage in Guilford
4.99 out of 5 average rating, 103 reviews

Waterfront Joshua Cove Cottage with private beach.

KitRating, 5 stars1 week ago
A truly lovely spot! Quiet, relaxing and comfortable. We enjoyed the view of the water, reading on the patio in the lounge chairs and sitting on the bench overlooking the beach. We would love to come back again.
Top guest favorite
Cottage in Ledyard
4.91 out of 5 average rating, 112 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

OliviaRating, 5 stars1 month ago
My sister, dog and I stayed at the cottage for the weekend and had a great experience! Erika is a wonderful host and the property is beautiful. The cottage itself was exactly as pictured. Breakfast in the inn, cooked with natural and organic ingredients, is an absolute must. The location of the inn is great as well, with direct access to the Lantern Hill trail (which our dog loved) and only a short drive from downtown. Would definitely recommend staying here!
Top guest favorite
Cottage in Guilford
4.94 out of 5 average rating, 271 reviews

The Cottage at Indian Cove

TaraRating, 5 stars3 days ago
This was a lovely cottage and location, part of a private beach community, on a very quiet road, with partial views of the Long Island Sound. Gail was thoughtful to put out a nice welcome basket and some cold sodas and bottle water in the fridge. Perfect spot for two to three people. Close to Guilford main green, dock and nearby Stony Creek and Madison. We didn't make use of the bikes and kayaks bc it rained in the mornings, but we enjoyed one of the two beach just a few minute walk away. Jacob's cove area is a gem.
Guest favorite
Cottage in East Haddam
4.9 out of 5 average rating, 131 reviews

Direct Waterfront Cottage on Moodus Reservoir.

WendyRating, 5 stars4 weeks ago
Nice little spot with boats on the pond. Went there for my son’s Wesleyan graduation and could take family out on the kayaks.
Guest favorite
Cottage in Lebanon
4.87 out of 5 average rating, 151 reviews

Go Jump in the Lake!

TimurRating, 5 stars2 days ago
Great property in a great location with great and very responsive host. Highly recommended.
Guest favorite
Cottage in Montville
4.95 out of 5 average rating, 106 reviews

Beautiful lakefront retreat just 15 mins to casino

NicoleRating, 5 stars1 month ago
Fantastic! The cottage is cozy and clean, had everything we needed and the views are gorgeous! We loved our stay and highly recommend this beautiful cottage!
Guest favorite
Cottage in Guilford
4.86 out of 5 average rating, 42 reviews

Your own Thimble Islands private cottage!

GailRating, 5 stars1 month ago
We had a fabulous weekend at this lovely cottage. Located on a remote peninsula surrounded by the glistening water we couldn’t have asked for a nicer experience. The amenities were both convenient and thoughtful. Although we chose to dine out, the kitchen was very modern with upscale appliances and an espresso machine. We did bbq on our last night and had a great end to our 4 night stay!

Cabin rentals with a kayak

Top guest favorite
Cabin in New Milford
5 out of 5 average rating, 8 reviews

Lakefront cabin with private dock on stunning cove

AlekseyRating, 5 stars9 months ago
We stayed here for 7 days with 2 small kids (2 and 4 years old) and wow was it amazing. The home is spacious and has everything we needed inside and outside the house. I could not have asked for anything else from the home and the dock was just so awesome to have, even caught 10+ fish right off the side. We rented a boat for a day from a marina and were able to come in and out of the backyard/house with no problems. I wish we could stay here for a whole month, but have to go back to real life!
Superhost
Cabin in Lebanon
4.89 out of 5 average rating, 18 reviews

Casa Lago

JasonRating, 5 stars4 weeks ago
A wonderful cozy little place to stay! We will definitely look you up again when we are back in the area!
Guest favorite
Cabin in North Stonington
4.93 out of 5 average rating, 43 reviews

Lakeside Landing

KatherineRating, 5 stars1 day ago
We had the most peaceful, relaxing weekend at lakeside landing! The house itself is a 10 out of 10, absolutely adorable and had everything we could possibly need. The bed was sooo comfy and the views are just amazing! We enjoyed paddling around the lake during the day and the fire pit and hot tub at night! We didn’t leave the house once!! Highly recommend:)
Guest favorite
Cabin in Bethlehem
4.9 out of 5 average rating, 31 reviews

Swim, fish, kayak & RELAX!

GeraldRating, 5 stars4 weeks ago
We stayed for a graduation near by, it was perfect for we were looking for. I wish the weather would have been a bit warmer to enjoy the water.
Top guest favorite
Cabin in Bethlehem
4.95 out of 5 average rating, 83 reviews

Cabin by the lake I Private Beach I Paddle Board

RebeccaRating, 5 stars2 days ago
The Cabin by the lake, was the perfect spot for a girls getaway. Mariana offered a detailed guide book, which was extremely helpful. Beautifully decorated home, with lots of those extra amenities that you didn't think you needed, but was pleasantly surprised that she offered. Quickly responded to any requests and offered helpful suggestions when needed. Highly recommend to anyone looking for a quaint, cozy and adorable home away from home.
Guest favorite
Cabin in Colebrook
4.94 out of 5 average rating, 95 reviews

Rustic Cabin+ Private Beach Pond, Stars & Wildlife

EdwardRating, 5 stars3 weeks ago
Amazing cabin!! My third visit. Was there with friends for fishing and I love the cabin so much that I booked my anniversary weekend and my wife is also in love with the property. Relaxing Birding Fishing Kayaking Fire pit Romantic This place has it all! Book it now! You won’t regret it!
Guest favorite
Cabin in Coventry
4.88 out of 5 average rating, 137 reviews

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Rebecca ChantelRating, 5 stars4 days ago
The lake house is absolutely charming. We easily made our way around Coventry and UCONN. We enjoyed our evenings overlooking the lake. Our favorite was definitely the record player and disco lights, the neighbors hopefully enjoyed the light show through the windows!! lol Thank you for a great stay, see you again soon
Guest favorite
Cabin in New Hartford
4.98 out of 5 average rating, 50 reviews

West Hill Cabin

ChrisRating, 5 stars2 months ago
Great location near West Hill Lake and Brodie Park; walking distance to public beach, playground, and more. The house is very clean and well provisioned. A great stay!

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